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Preparation method of o-aminoacetophenone

A technology of o-aminoacetophenone and o-nitroethylbenzene, which is applied in the field of preparation of o-aminoacetophenone, achieves the effects of sufficient supply, cost saving, and simple preparation steps

Pending Publication Date: 2020-03-31
NANJING JIEYUN PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In order to solve the problems existing in the preparation method of o-aminoacetophenone, the relevant manufacturers have tried their best to find a solution, but no suitable design has been developed for a long time, and the general method cannot solve the above problems. This is obviously a problem that relevant industry players are eager to solve

Method used

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  • Preparation method of o-aminoacetophenone
  • Preparation method of o-aminoacetophenone
  • Preparation method of o-aminoacetophenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Add 80.0g o-nitroethylbenzene, 800mL DMF, 143.59g sodium chlorite, 63.59g acetic acid solution (50% content) into the three-necked flask and mix, then heat the mixed solution to 60-70°C for 20h, the reaction After cooling the final solution, quench the reaction with saturated sodium sulfite solution, then extract twice with ethyl acetate (1500mL*2), combine the ethyl acetate layer, wash once with saturated brine, and dry the organic phase with anhydrous sodium sulfate , concentrated, and the residue was distilled under reduced pressure to obtain 54.2 g of pure o-nitroacetophenone with a purity greater than 95%, with a yield of 62.01%.

[0049] Add 542mL of ethanol and 2.7g of palladium carbon to the obtained o-nitroacetophenone, at 50°C, 1MPa H 2 Hydrogenate under pressure for 12 hours, filter to remove palladium carbon, and rectify the filtrate to obtain o-aminoacetophenone with a purity greater than 99%.

Embodiment 2

[0051] Add 80.0g o-nitroethylbenzene, 800mL DMF, 264.97g sodium perbromate, 259.3g phosphoric acid solution (20% content) into the three-necked flask, then heat the mixed solution to 60-70°C for 20h, and put the reaction After the solution was cooled, the reaction was quenched with saturated sodium sulfite solution, extracted twice with ethyl acetate (1500mL*2), the combined ethyl acetate layer was washed once with saturated brine, and the organic phase was dried with anhydrous sodium sulfate. After concentration, the residue was distilled under reduced pressure to obtain 59.3 g of pure o-nitroacetophenone with a purity greater than 95%, with a yield of 67.85%.

[0052] Add 593mL of ethanol and 12g of Raney nickel to the o-nitroacetophenone in the above step, at 70°C, 1MPa H 2 Hydrogenate under pressure for 12 hours, remove Raney nickel by filtration, and rectify the filtrate to obtain o-aminoacetophenone with a purity greater than 99%.

Embodiment 3

[0054] Add 80.0g o-nitroethylbenzene, 800mL acetone, 264.97g sodium perbromate, 259.3g phosphoric acid solution (20% content) into the three-necked flask, then heat the mixed solution to 60-70°C for 20h, and the reaction After the solution was cooled, the reaction was quenched with saturated sodium sulfite solution, extracted twice with ethyl acetate (1500mL*2), the combined ethyl acetate layer was washed once with saturated brine, and the organic phase was dried with anhydrous sodium sulfate. After concentration, the residue was distilled under reduced pressure to obtain 48.5 g of pure o-nitroacetophenone with a purity greater than 95%, with a yield of 55.4%.

[0055] Add 485mL of methanol and 2.4g of palladium carbon to the o-nitroacetophenone in the above step, at 40°C, 1MPa H 2 Hydrogenate under pressure for 12 hours, filter to remove palladium carbon, and rectify the filtrate to obtain o-aminoacetophenone with a purity greater than 99%.

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Abstract

The invention discloses a preparation method of o-aminoacetophenone. The preparation method comprises the following steps: (1) mixing o-nitroethylbenzene, an oxidant, a cocatalyst and an organic solvent, heating the obtained mixed solution to a certain temperature for a reaction, and subjecting the reacted solution to cooling, quenching and extracting to obtain o-nitroacetophenone; and (2) addinga polar solvent and a metal catalyst into the obtained o-nitroacetophenone, carrying out a hydrogenation reduction reaction to obtain a crude o-aminoacetophenone product, and filtering and rectifyingthe crude o-aminoacetophenone product to obtain a refined o-aminoacetophenone product. According to the invention, used raw materials are low in price and easy to obtain, and steps are simple and easyto operate. The o-aminoacetophenone obtained by the method disclosed by the invention is high in purity and high in yield.

Description

technical field [0001] The invention relates to the technical field of organic intermediate synthesis, in particular to a preparation method of o-aminoacetophenone. Background technique [0002] O-aminoacetophenone is an important fine chemical intermediate, which is widely used in the synthesis of pesticide and pharmaceutical intermediates. It is the main raw material of anti-infective quinolones, and quinolones are one of the hot spots in drug research today. [0003] At present, the main source of o-aminoacetophenone supplied industrially in the market is hydrogenated o-nitroacetophenone, and o-nitroacetophenone itself is also an important pharmaceutical intermediate, used as a sensitizer for photosensitive resins , widely used in the chemical industry. The main source of o-nitroacetophenone in the market is the industrial by-product of p-nitroacetophenone. With the sharp drop in demand for downstream products of p-nitroacetophenone, the shortage of production has result...

Claims

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Application Information

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IPC IPC(8): C07C221/00C07C225/22
CPCC07C201/12C07C221/00C07C205/45C07C225/22
Inventor 周禾方靖舒恺宋兴昌张力余增辉吴晓东刘郝敏
Owner NANJING JIEYUN PHARMA TECH CO LTD
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